Novel benzimidazole-acrylonitrile hybrids and their derivatives: Design, synthesis and antimycobacterial activity

Sirim, Mustafa Mert; Krishna, Vagolu Siva; Sriram, Dharmarajan; Tan, Oya Ünsal

doi:10.1016/j.ejmech.2019.112010

Cited by 35 publications

(20 citation statements)

References 29 publications

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“…As typically important bioactive heterocyclic compounds, benzimidazoles have been extensively investigated for their broad spectrum in biological and pharmacological activities in antibacterial, antifungal, antiviral, anti-inflammatory, anti-ulcer, antihypertensive, antihistamine, antitumor, anticancer, and anti-HIV. [39][40][41][42][43][44] Therefore, various synthetic methods were developed. [45][46][47][48] However, these synthetic processes generally suffer from various limitations such as the use of strong acidic reaction medium, toxic solvents, high reaction temperature, reactive reagent, strong dehydrating agent, oxidizing agent, and noble metal catalysts.…”

Section: Introductionmentioning

confidence: 99%

H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

et al. 2020

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Co nanoparticles (NPs) encapsulated in N‐doped carbon nanotubes (Co@NC900) are systematically investigated as a potential alternative to precious Pt‐group catalysts for hydrogenative heterocyclization reactions. Co@NC900 can efficiently catalyze hydrogenative coupling of 2‐nitroaniline to benzaldehyde for synthesis of 2‐phenyl‐1H‐benzo[d]imidazole with >99 % yield at ambient temperature in one step. The robust Co@NC900 catalyst can be easily recovered by an external magnetic field after the reaction and readily recycled for at least six times without any evident decrease in activity. Kinetic experiments indicate that Co@NC900‐promoted hydrogenation is the rate‐determining step with a total apparent activation energy of 41±1 kJ mol−1. Theoretical investigations further reveal that Co@NC900 can activate both H2 and the nitro group of 2‐nitroaniline. The observed energy barrier for H2 dissociation is only 2.70 eV in the rate‐determining step, owing to the presence of confined Co NPs in Co@NC900. Potential industrial application of the earth‐abundant and non‐noble transition metal catalysts is also explored for green and efficient synthesis of heterocyclic compounds.

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Section: Introductionmentioning

confidence: 99%

H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

et al. 2020

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“…Ridinazole, another benzimidazole compound, was used as a novel antibacterial agent against Clostridium difficile ( Cho et al, 2019 ). Besides, the benzimidazole-based scaffold has been shown to have anti-mycobacterial activity, making it a promising structure for the discovery of new anti-TB agents ( Keri et al, 2016 ; Sirim et al, 2020 ; Parwani et al, 2021 ). However, there were no biological activities reported on F0414 in the previous studies.…”

Section: Discussionmentioning

confidence: 99%

Screening and Identification of a Novel Anti-tuberculosis Compound That Targets Deoxyuridine 5′-Triphosphate Nucleotidohydrolase

Zhang

Chen

et al. 2021

Front. Microbiol.

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Tuberculosis (TB) is still a threat to humans worldwide. The rise of drug-resistant TB strains has escalated the need for developing effective anti-TB agents. Deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase) is essential for thymidylate biosynthesis to maintain the DNA integrity. In Mycobacterium tuberculosis, dUTPase provides the sole source for thymidylate biosynthesis, which also has the specific five-residue loop and the binding pockets absent in human dUTPase. Therefore, dUTPase has been regarded as a promising anti-TB drug target. Herein, we used a luminescence-based dUTPase assay to search for the inhibitors target M. tuberculosis dUTPase (Mt-dUTPase) and identified compound F0414 as a potent Mt-dUTPase inhibitor with an IC50 of 0.80 ± 0.09 μM. F0414 exhibited anti-TB activity with low cytotoxicity. Molecular docking model and site-directed mutation experiments revealed that P79 was the key residue in the interaction of Mt-dUTPase and F0414. Moreover, F0414 was shown to have stronger binding with Mt-dUTPase than with Mt-P79A-dUTPase by surface plasmon resonance (SPR) detection. Interestingly, F0414 exhibited insensitivity and weak directly binding on human dUTPase compared with that on Mt-dUTPase. All the results highlight that F0414 is the first compound reported to have anti-TB activity by inhibiting Mt-dUTPase, which indicates the potential application in anti-TB therapy.

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“…Sirim et al designed and synthesized benzimidazole-acrylonitrile hybrid derivatives from benzene-1, 2-phenyleneamine and ethyl cyanoacetate followed by reaction with piperazines [78]. All the derived compounds exhibited anti-mycobacterial activity against M. tuberculosis H37Rv strain by microplate alamar blue assay (MABA).…”

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

Kavya¹,

Sivan²

2022

Benzimidazole

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Benzimidazole, one of the finest classes of heterocyclic aromatic compounds have the characteristic structure of benzene fused with a five-membered imidazole ring. Despite being made their first appearance in the late 1870s, they are considered as a ‘privileged molecule’. The applications of this wonder molecule range from medicinal chemistry to material science. Benzimidazole being a potent inhibitor for various enzymes has got therapeutic effects like anticancer, antimicrobial, anthelmintic, antioxidant, anticonvulsant, antifungal, anti-inflammatory, antiviral, antihistaminic, antipsychotic, etc. It has also made its existence in various branches of medical science viz ophthalmology, neurology, cardiology and more. The applications of benzimidazole are not only limited to the biological field but also expanded to the field of material chemistry as well. This chapter summarizes the pharmacological properties of benzimidazole, illustrated on numerous derivatives since 2016.

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Novel benzimidazole-acrylonitrile hybrids and their derivatives: Design, synthesis and antimycobacterial activity

Cited by 35 publications

References 29 publications

H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

Screening and Identification of a Novel Anti-tuberculosis Compound That Targets Deoxyuridine 5′-Triphosphate Nucleotidohydrolase

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

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Novel benzimidazole-acrylonitrile hybrids and their derivatives: Design, synthesis and antimycobacterial activity

Cited by 35 publications

References 29 publications

H2 Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

H2 Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

Screening and Identification of a Novel Anti-tuberculosis Compound That Targets Deoxyuridine 5′-Triphosphate Nucleotidohydrolase

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

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H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

H₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles